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Synthesis of aryl 2‐(2‐imidazolyl)ethyl ketones
Author(s) -
Abdelaal Salma M.,
Kim JangWoo,
Bauer Ludwig
Publication year - 1995
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570320338
Subject(s) - chemistry , sodium borohydride , aryl , catalysis , medicinal chemistry , hydrolysis , platinum , organic chemistry , alkyl
The Claisen‐Schmidt condensation of 1‐(triphenylmethyl)‐2‐imidazolecarboxaldehyde with acetophenones yielded 1‐aryl‐3‐[1‐(triphenylmethyl)‐2‐imidazolyl]propen‐1‐ones 7 . Selective catalytic hydrogenation over platinum of 7 furnished 1‐aryl‐3‐(2‐imidazolyl)‐1‐propanones 8 . An alternate synthesis of 8 started with sodium borohydride reduction of 7 to give allylic alcohols, 1‐aryl‐3‐[1‐(triphenylmethyl)‐2‐imidazolyl]‐2‐propen‐1‐ols 10 , which were rearranged by hot aqueous sodium to 8 . Acid hydrolysis of 8 provided the title compounds and triphenylmethanol.